(1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

Base Information

Chemical Name:(1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one
CAS No.:1260612-97-2
Molecular Formula:C₃₄H₅₄O₄Si
Molecular Weight:554.886
Hs Code.:

Synonyms:(1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

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Chemical Property of (1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

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Technology Process of (1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

There total 26 articles about (1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: (S)-1-((1R,3S,4R)-2-((4-methoxybenzyloxy)methylene)-3,4-dimethyl-3-(3-methylnona-3,8-dienyl)cyclohexyl)-3-methyl-3-(triethylsilanyloxy)oct-6-en-1-one

: (1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

: 1260612-97-2
(1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

Guidance literature:: With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 4h; optical yield given as %de;
DOI:10.1021/ol1026816

Reference yield:

: 1260612-73-4
(1R,5R)-1-ethyl 2-methyl 5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopent-2-ene-1,2-dicarboxylate

: (1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

: 1260612-97-2
(1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

Guidance literature:: Multi-step reaction with 14 steps

1.1: diisobutylaluminium hydride / hexane / 4 h / -78 - 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

2.2: 15 h / 0 - 20 °C

3.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve

4.1: hydrazine / ethylene glycol / 0.5 h / 130 °C

4.2: 3 h / 230 °C

5.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 16 h / 45 °C

6.1: benzene / 16 h / 45 °C

7.1: water; toluene-4-sulfonic acid / tetrahydrofuran / 16 h / 20 °C

8.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C

8.2: 2 h / 0 - 20 °C

9.1: water; potassium hydroxide / 1,4-dioxane / 4 h / 65 °C

10.1: lead(IV) tetraacetate; potassium carbonate / benzene / 0.33 h / 20 °C

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

11.2: 0.5 h / 0 °C

12.1: (triphenylphosphine)copper hydride hexamer / toluene / 4 h / -40 - 20 °C

13.1: pyridine; thionyl chloride / 0.5 h / 0 °C

14.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / 40 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; n-butyllithium; thionyl chloride; tetrapropylammonium perruthennate; (triphenylphosphine)copper hydride hexamer; water; lead(IV) tetraacetate; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; potassium hydroxide; hydrazine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; ethylene glycol; toluene; mineral oil; tert-butyl alcohol; benzene; 4.2: Wolff-Kishner reduction / 8.2: Wittig reaction / 11.2: Horner-Wadsworth-Emmons olefination / 12.1: Aldol condensation / 14.1: Ring-closing metathesis;
DOI:10.1021/ol1026816

Reference yield:

: 1260612-74-5
(1R,5R)-5-methyl-1-(2-(2-methyl-1,3-dioxolan-2-yl)ethyl)cyclopent-2-ene-1,2-diyl-dimethanol

: (1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

: 1260612-97-2
(1R,4S,11S,12R,7Z)-15-((4-methoxybenzyloxy)methylene)-4,8,11,12-tetramethyl-4-(triethylsilanyloxy)bicyclo(9.3.1)pentadec-7-en-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C

1.2: 15 h / 0 - 20 °C

2.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.5 h / 20 °C / Molecular sieve

3.1: hydrazine / ethylene glycol / 0.5 h / 130 °C

3.2: 3 h / 230 °C

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 16 h / 45 °C

5.1: benzene / 16 h / 45 °C

6.1: water; toluene-4-sulfonic acid / tetrahydrofuran / 16 h / 20 °C

7.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / 0 °C

7.2: 2 h / 0 - 20 °C

8.1: water; potassium hydroxide / 1,4-dioxane / 4 h / 65 °C

9.1: lead(IV) tetraacetate; potassium carbonate / benzene / 0.33 h / 20 °C

10.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / 0 °C

10.2: 0.5 h / 0 °C

11.1: (triphenylphosphine)copper hydride hexamer / toluene / 4 h / -40 - 20 °C

12.1: pyridine; thionyl chloride / 0.5 h / 0 °C

13.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 4 h / 40 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; n-butyllithium; thionyl chloride; tetrapropylammonium perruthennate; (triphenylphosphine)copper hydride hexamer; water; lead(IV) tetraacetate; sodium hexamethyldisilazane; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; potassium hydroxide; hydrazine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; ethylene glycol; toluene; mineral oil; tert-butyl alcohol; benzene; 3.2: Wolff-Kishner reduction / 7.2: Wittig reaction / 10.2: Horner-Wadsworth-Emmons olefination / 11.1: Aldol condensation / 13.1: Ring-closing metathesis;
DOI:10.1021/ol1026816